Tetrahydrofuran → HCID 118037657, compound

HRID 2272506Notes

Reaction equation

HRID 2272506 reaction equation
C([Li])CCC.C1C[O:9][CH2:8]C1.[F:11][C:12]1[C:17]([O:18][CH2:19][O:20][CH3:21])=[CH:16][CH:15]=[CH:14][C:13]=1[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1.[Cl-].[NH4+]>CN(C=O)C>[F:11][C:12]1[C:17]([O:18][CH2:19][O:20][CH3:21])=[C:16]([CH:8]=[O:9])[CH:15]=[CH:14][C:13]=1[C:22]1[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 904236412,4′-Difluoro-3-(methoxymethoxy)-1,1′-biphenylHCID 178418339Butyllithium

Product 1

HCID 118037657HCID 118037657, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

n-Butyllithium (1.6 M hexane solution, 52.2 mL) was added at −78 C to an anhydrous THF (200 mL) solution of 2,4′-difluoro-3-(methoxymethoxy)biphenyl (19.0 g) in an argon atmosphere, and then, the mixture was stirred at −78 C for 1 hour. DMF (12.9 mL) was added thereto, and then, the mixture was stirred for 3 hours in an argon atmosphere while heated from −78 C to 0 C. A saturated aqueous solution of ammonium chloride was added to the reaction mixture at room temperature, followed by extraction with ethyl acetate. The organic layer was separated, then washed with saturated saline, and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was solidified with hexane to obtain the title compound (16.4 g).

Workup

  1. stirringthe mixture was stirred for 3 hours in an argon atmosphere
  2. temperaturewhile heated from −78 C to 0 C
  3. extractionfollowed by extraction with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-74d3b1e4b91f4c5e9994c78ca8bfc8f0
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

Loading…